Information on EC 2.5.1.122 - 4-O-dimethylallyl-L-tyrosine synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.5.1.122
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RECOMMENDED NAME
GeneOntology No.
4-O-dimethylallyl-L-tyrosine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + L-tyrosine = diphosphate + 4-O-dimethylallyl-L-tyrosine
show the reaction diagram
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-
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SYSTEMATIC NAME
IUBMB Comments
dimethylallyl diphosphate:L-tyrosine 4-O-dimethylallyltransferase
The enzyme is involved in biosynthesis of the phytotoxin sirodesmin PL by the phytopathogenic ascomycete Leptosphaeria maculans.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
?
show the reaction diagram
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98% activity compared to 3-iodo-L-tyrosine
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-
?
dimethylallyl diphosphate + 3-amino-L-tyrosine
diphosphate + 3-amino-4-O-dimethylallyl-L-tyrosine
show the reaction diagram
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SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives. 3-Amino-L-tyrosine is prenylated with 108% of the activity compared to L-tyrosine
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-
?
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
?
show the reaction diagram
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53% activity compared to 3-iodo-L-tyrosine
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-
?
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 4-O-dimethylallyl-3-fluoro-DL-tyrosine
show the reaction diagram
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SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives. 3-Iodo-L-tyrosine is prenylated with 53.6% of the activity compared to L-tyrosine
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-
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
?
show the reaction diagram
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100% activity
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-
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + 4-O-dimethylallyl-3-iodo-L-tyrosine
show the reaction diagram
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SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives. 3-Iodo-L-tyrosine is prenylated with 27.3% of the activity compared to L-tyrosine
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-
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
?
show the reaction diagram
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23% activity compared to 3-iodo-L-tyrosine
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-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
?
show the reaction diagram
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13% activity compared to 3-iodo-L-tyrosine
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-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 7-dimethylallyl-4-methyl-L-tryptophan
show the reaction diagram
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41% activity compared to 3-iodo-L-tyrosine
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-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 7-dimethylally-5-methyl-L-tryptophan
show the reaction diagram
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10% activity compared to 3-iodo-L-tyrosine
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-
?
dimethylallyl diphosphate + alpha-methyl-L-tyrosine
?
show the reaction diagram
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98% activity compared to 3-iodo-L-tyrosine
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-
?
dimethylallyl diphosphate + D-tyrosine
?
show the reaction diagram
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33% activity compared to 3-iodo-L-tyrosine
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-
?
dimethylallyl diphosphate + L-3,4-dihydroxyphenylalanine
?
show the reaction diagram
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16.6% of the activity, compared to L-tyrosine. It is expected that the prenylation takes place at the 4-hydroxyl group. The structure of the product is not determined
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?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 1-(2-methylbut-3-en-2-yl)-L-tryptophan
show the reaction diagram
reverse prenylation
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-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-dimethylallyl-L-tryptophan
show the reaction diagram
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33% activity compared to 3-iodo-L-tyrosine
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?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-dimethylallyltryptophan
show the reaction diagram
catalytic efficiency for L-tryptophan is 6% compared to catalytic efficiency for L-tyrosine
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?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
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5 mM, 1.4fold activation compared to activity without additives
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
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5 mM, 12% inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.19
3,4-dihydroxy-L-phenylalanine
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at pH 7.5 and 37C
0.29
3-iodo-L-tyrosine
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at pH 7.5 and 37C
0.25 - 0.69
4-methyl-DL-tryptophan
0.42
alpha-Methyl-L-tyrosine
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at pH 7.5 and 37C
0.22
D-tyrosine
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at pH 7.5 and 37C
0.17 - 0.71
dimethylallyl diphosphate
0.19 - 0.37
L-tryptophan
0.13 - 0.3
L-tyrosine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.27
3,4-dihydroxy-L-phenylalanine
Aspergillus niger
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at pH 7.5 and 37C
0.16
3-iodo-L-tyrosine
Aspergillus niger
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at pH 7.5 and 37C
0.0036 - 0.2
4-methyl-DL-tryptophan
0.26
alpha-Methyl-L-tyrosine
Aspergillus niger
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at pH 7.5 and 37C
0.16
D-tyrosine
Aspergillus niger
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at pH 7.5 and 37C
0.69
dimethylallyl diphosphate
Aspergillus niger
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with 3-iodo-L-tyrosine as cosubstrate, at pH 7.5 and 37C
0.0053 - 0.095
L-tryptophan
0.58 - 1.3
L-tyrosine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.421
3,4-dihydroxy-L-phenylalanine
Aspergillus niger
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at pH 7.5 and 37C
2636
0.551
3-iodo-L-tyrosine
Aspergillus niger
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at pH 7.5 and 37C
2332
0.043 - 0.8
4-methyl-DL-tryptophan
11621
0.619
alpha-Methyl-L-tyrosine
Aspergillus niger
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at pH 7.5 and 37C
43744
0.727
D-tyrosine
Aspergillus niger
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at pH 7.5 and 37C
1643
0.972
dimethylallyl diphosphate
Aspergillus niger
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with 3-iodo-L-tyrosine as cosubstrate, at pH 7.5 and 37C
157
0.028 - 0.26
L-tryptophan
119
4.3 - 7.7
L-tyrosine
109
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
100000
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His6-tagged enzyme, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 52700, calculated from amino acid sequence
dimer
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2 * 50000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
overexpression in Escherichia coli
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overproduction of His6-SirD in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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the specific 4-O-prenylation of tyrosine derivatives by SirD could find usage for production of prenylated tyrosine derivatives by chemoenzymatic synthesis